


Desperately Seeking Someone

by cleflink



Category: Supernatural RPF
Genre: Alternate Universe, Alternate Universe - Modern Setting, Friends to Lovers, M/M, Unorthodox Dating Techniques
Language: English
Status: Completed
Published: 2017-12-01
Updated: 2017-12-01
Packaged: 2019-02-09 01:26:53
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 9,119
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12877248
Author URL: https://archiveofourown.org/users/cleflink/pseuds/cleflink
Summary: After the dramatic implosion of yet another relationship, Jensen is ready to swear off love forever. Instead, he ends up trying to find a new boyfriend with what is perhaps the most unorthodox method known to man. He’ll never live it down if it actually works.As it turns out, Fate has a funny way of showing him that what he thought he'd been missing all along… isn't quite what he expected.





	Desperately Seeking Someone

**Author's Note:**

> Written for the 2017 round of spn_reversebang. 
> 
> RBB is one of my favourite challenges, because we have so many talented artists in this fandom, and I love the chance to get to work with new people and stretch my writing muscles to write to a visual prompt. This is the first time since I started participating that there was One Prompt that I wanted above all others, so I was beyond lucky to claim dancing_adrift's incredibly inspiring art. She has been a great partner to work with - even when I wasn't such a good partner to her - and her enthusiasm for this collab was infectious. I can only hope that I've done her fantastic art justice, and I hope that you all go visit her Art Post to give her some well-deserved kudos! It was great working with you, hon!
> 
> Thanks also to our lovely mods, for all the hard work they do keeping this challenge running smoothly.

It was official. Jensen was going to be alone forever.

Chris snorted. "Jesus, you're such a drama queen. So your boyfriend was a dickbag. Shit happens. Pick someone better next time."

Jensen lifted his head out of the pillow of his arms to glare at him. "Easy for you to say."

"Why, because I'm not a drama queen?"

"Chris," Danneel admonished. "You're not helping."

"I'm not trying to help." Chris gestured at Jensen's sad sprawl across the table. "God knows, I tried to help the first dozen times this happened, but it all starts getting old after a while. Jensen should stop having such shit taste in men."

"It's not like I mean to have shit taste in men," Jensen protested. "I'd like nothing better than to find the 'right one' or whatever. But God, it's just like..." He flailed a hand in the air. "Every time I think I've got something good going on, he turns out to be a jerk, or he cheats on me or we fall out of love or..." He huffed, slumping back onto the table. "Fuck everything."

"Maybe you need to change your type," Danneel suggested. "Prioritize something other than the fact that they're hot."

Jensen shot her a wounded look. "Hey, I have more standards than hotness."

"He also likes it when they're bigger than him," Steve chimed in, and was ready with an innocent look when Jensen glared at him.

"What, so I should start with 'likes dogs' or something? Knowing my luck, it'd end in some bestiality thing."

Chris, who'd just taken a swallow of beer, nearly choked on it. Which, Jensen had to admit, did make him feel a little better. "Fucker," Chris scowled, wiping his chin. 

"I'm just saying," Danneel continued, still mysteriously sober. She'd been so much better at joining in on Jensen's pity parties back in college. "These guys you're meeting at the gym clearly aren't working out for you. You need a new approach."

"Like what?"

"Have you tried online dating?" Steve suggested.

"Yep," Jensen said, emphasizing the snap of the p. "Fuck, I've tried everything except putting up wanted posters. And what do I have to show for it? Fucking nothing."

"Don't go giving up on the world just yet," Danneel tried.

"Don't see why not," Jensen muttered. Danneel raised an eyebrow at him and he sighed. "Can we stop trying to fix my disastrous love life and start focusing on getting me drunk enough not to remember this conversation in the morning?"

"You're finally talking sense," Chris said approvingly. "Now _that_ I can help with."

Chris was true to his word. Jensen spent the rest of the evening getting completely shitfaced and then passed out on the couch after his friends caught a cab home.

He wished he could say that this was an unusual occurrence, but Chris sadly hadn't been exaggerating about how often his relationships crashed and burned.

Jensen shamelessly called in sick the next morning, then staggered to bed and slept for another four hours. He woke up again around noon and proceeded to spend the rest of the day nursing his hangover and feeling sorry for himself. His apartment seemed agonizingly big and empty with just him in it, and never mind that James had never actually lived there. It felt... symbolically empty, or whatever. Just like it always seemed to after he broke up with yet another boyfriend.

Maybe he should get a dog. At least a dog would love him.

Just after six, there was the unexpected scrape of a key in the lock.

"You dead?" Danneel's familiar voice called as she walked into the apartment, and Jensen relaxed from his instinctive panic.

Not that that meant he was in the mood for company, though.

"Yes!" he shouted back. "Go away!"

"If you didn't want me to check on you when you're moping, you shouldn't have given me a key!" There were the twin thumps of Danneel's shoes hitting the floor, and the clink of her keys on the side table. "Besides, I brought pizza!"

Jensen's stomach, traitor that it was, gurgled at the thought.

"I'm in the den!" he called, resigned. 

"Well," Danneel said, as she appeared in the doorway a moment later, bearing two boxes of pizza. "You've looked worse, at least. Move over."

"How kind," Jensen said dryly, shifting across the couch to give Danneel room to sit. He rolled his head towards her. "Don't you usually bother Genevieve on Mondays?"

"Usually," Danneel agreed. "But she's busy helping Jared with some stuff he's going through."

"Ah," Jensen said, nodding in understanding. 

Jared was to Genevieve what Jensen was to Danneel. Jensen didn't really know him very well - beyond trash-talking each other's basketball teams at events when their whole, massively extended friends group got together, of course - but he did know that Jared wasn't the type to ask for help needlessly. If he needed Genevieve, he could understand why Danneel wasn't pissed about the loss of her girls' night. 

Not that that meant Jensen was all that happy about Danneel interrupting _his_ personal pity party instead. "So you decided to inflict yourself on me instead? Some friend you are."

"Bitch, I'm the best friend you've got," Danneel said, unbothered.

"That is a sad, sad reflection on my life."

"Probably. You should drown your sorrows in pizza before you waste away entirely."

Jensen heaved a put-upon sigh. "Yes, mom," he said, reaching out for a slice.

The first bite was enough to remind him that he was ravenous, and he practically inhaled the rest of it. Danneel wordlessly tilted the box towards him, and Jensen didn't even bother complaining as he reached for another.

He put away half a pizza without bothering to come up for air, and felt his tension easing as the grease helped smooth out the lingering traces of his hangover.

"Feeling better?" Danneel asked, when he finally slowed down.

"You're a goddess among women," Jensen answered, his tone falling somewhere between sarcastic and deadly serious. He fixed her with a look. "Are you going to tell me what you're doing here?"

Danneel lifted an eyebrow. "Isn't 'saving you from yourself' enough?"

Before she'd fed him, it would have been, but the lack of headache was enough to get Jensen's brain going again.

He gestured towards the remains of dinner. "No way do you buy two pizzas for just us unless you're trying to con me into something."

Danneel gave a rueful shake of her head. "You know, you're much easier to manage when you're hungover."

"Danni," Jensen chided. "Spill."

She huffed a sigh. "So, I was thinking about your dating crisis, and something you said yesterday gave me kind of an idea."

"Was it the giving up forever part?" Jensen asked. "Because that's pretty much where I'm at right now."

"Not exactly." She dug into her advertising portfolio, and how out of it had Jensen been that he hadn't even noticed her carrying it? The thing was practically the size of a car windshield. 

"Somehow, Danni, I don't think an ad for toothpaste is going to cheer me up, no matter how amazing it is."

"It's not for toothpaste," Danneel said, still rifling through papers. "It's - aha!" She pulled out a glossy, full colour poster and presented it with a flourish. "Ta da! What do you think?"

Jensen stared.

It was a flyer, the type he saw on bulletin boards at the rec centre around the corner. And it was advertising...

"Is this a want ad for a boyfriend?" Jensen demanded, staring with a horrified sort of fascination at the picture of himself looking out from underneath a striped umbrella with a bullet list of desired boyfriend traits running down the side. The word MISSING was scrawled in bold red letters across the top. "No, wait. Is this a _lost dog_ ad for a boyfriend? The hell are you doing at work these days?"

"Designing big important posters for big important companies." She somehow managed to smirk kindly as she added, "And little posters for pathetic best friends."

Jensen was still staring at the list of boyfriend traits. _Kind, funny, smart, stabl_ , Christ, she might as well have been asking for the moon: no way any guy with that kind of CV wouldn't already be taken. "Where did you get even that picture of me?"

Danneel shrugged. "Facebook. So? What do you think?"

"Are you actually suggesting that I advertise for a boyfriend with a lost dog poster?"

"Yes, I really am."

"No," Jensen said immediately.

Danneel's mouth curled into a pout. "You haven't even thought about it!"

"A thousand times no. This is not the way to find a date."

"Why not?" she asked, as though this was a remotely sane thing to be discussing. "It's not that much different from the personal ads that newspapers used to run. Or from online dating, for that matter."

"Neither of which have worked out for me, I'll thank you to remember."

"You just had some bad luck, that's all! Jensen." She grabbed his hand and, dammit, there went the pleading face. "I just hate seeing you so unhappy. And at least you haven't had any bad experiences with dating via wanted ad."

"That's because it's a terrible idea and no one in their right mind would attempt it!" Jensen retorted, waving his arms a bit for emphasis.

She looked at him with sad eyes. "Is it really so bad that I'm trying to help?"

Jensen deflated embarrassingly fast. "No, of course not. But seriously Danni, a _want ad_?" He huffed out a laugh. "I'm going to look like a desperate lunatic."

"Because I'm your friend, I'm going to let that one pass without comment."

"Gee thanks," Jensen said dryly. "We both know you're only letting it go because you want me to agree with this… this.... lunacy."

Danneel met his accusatory gaze without wavering. "You got a better idea? That isn't being pathetically alone for the rest of your life," she added, before Jensen could say just that.

And dammit, no he didn’t. 

"Please? Just give it a try."

"Fine," he surrendered, oofing as she gave an excited squeal and threw her arms around him. "But I still think it's a total waste of effort." He took another glance at the poster lying innocuously on the coffee table. "Seriously, that can't be what your degree in graphic design is supposed to be used for. How long did that take you?"

"Doesn't matter," Danneel said dismissively. She gave him a beaming smile. "Not when it's in the name of you finding true love."

"Um," Jensen said delicately. "You are emotionally prepared for this not working out, right? I mean, I doubt if anyone's even going to call."

Danneel's smile was entirely too smug. "Oh, we'll see about that. More pizza?"

Danneel, of course, was right.

She ran off a bunch of posters and Jensen spent a thoroughly embarrassing afternoon putting them up on bulletin boards in coffee shops, laundromats and gyms around town. He even put one up at his local rec centre, his hood pulled up and his sunglasses firmly on in the hopes that no one would recognize him. 

He survived the ordeal thankfully undetected, and then all there was left to do was wait.

In all honesty, Jensen had expected it to be a colossal waste of time. He figured he'd get a couple of prank calls, maybe even a dick pic or two, but nothing substantial. Because who the hell would be crazy enough to answering a 'lost boyfriend' ad? The whole idea was madness.

Then the calls started.

First a couple. Then with increasing momentum until, by the time the weekend arrived, his phone was ringing an average of once an hour. At least.

"You're pranking me, aren't you?" Jensen demanded of Danneel, brandishing his phone at her. His phone, which was still goddamn ringing with the latest hopeful responder. "It's like that one scene in _Mrs. Doubtfire_. You're making all of our friends call me with funny voices and stuff to make it seem like this idea isn't as insane as it really is."

"Nope," she said, with a relish that Jensen thought was totally uncalled for. "It's all you, baby."

Jensen scowled at her. "I hate you so much."

"You can thank me when you meet Mr. Right!" she said cheerily, and promptly stopped listening to him. Worst best friend ever.

Danneel's amazing unhelpfulness aside, the long and short of this whole debacle was that Jensen now had a decision to make. Was he actually going to go on dates with some of these guys?

After a long, mostly internal debate punctuated with spastically flailing arms and several eloquent 'the fucks?', Jensen ultimately decided to go for it. Like Danneel had said, it wasn't really all that different from online dating: the uncertainty, hint of risk and potential for utter disaster were all things he'd dealt with before. And why shouldn't he take advantage of all these guys who apparently liked the look of him even when he was doing crazy things like advertising for a missing boyfriend? At the very least it got him out of the house, and it might get him laid once or twice. 

Besides, Danneel would kick his ass if he responded by changing his phone number and moving to Mexico.

Thus decided, Jensen turned his attention to sorting through the impressive backlog of messages. He discarded most of them out of hand for being generally skeevy, a couple more that had been left by women (seriously?), and the expected collection of prank calls and dick pics, but there were a handful that seemed okay. 

Calling the first one back ranked high on Jensen's list of 'Things That I Wish Someone Was Making Me Do So It Wasn't My Fault That I Feel Like Such a Loser', but if he could fake interest in bi-monthly sales report meetings, then he could handle this without giving away just how much he wanted to fling the phone out the window and go hide under the covers for a decade or two.

He set up three dates for the coming weekend and then rewarded himself with his mama's recipe for loaded nachos with chili dip and a night of vegging out on the couch. It wasn't like he had anything to worry about, he reasoned to himself. They were just blind dates. With complete strangers who thought that answering a lost boyfriend ad was a smart thing to do.

Jensen was so fucked.

Though Jensen had never considered himself the sort of person who lacked confidence - well, not since puberty had been so nice to him, anyway - he changed his outfit no less than three times before leaving for his first scheduled date. Then he sat in his car in the parking lot for a good ten minutes trying to get up enough nerve to go inside instead of giving in to the urge to turn around and go the hell home.

God, when was the last time he'd been this nervous about a date? He wasn't sure he could remember.

Eventually, inevitably, Jensen managed to convince himself to get out of the car and into the coffee shop. He'd picked a place that was closer to Chris' apartment than his, just in case he needed a quick rescue. It was a homey, casual sort of place that put some of his nerves at ease.

His date was already there, lingering unsubtly to one side of the counter. Taking a breath, Jensen pasted on his first meeting smile and strode forward with hand extended.

"Jeff?" he asked, though he already knew full well, thanks to the picture he'd been sent earlier in the week. Jeff Morgan was about of a height with Jensen and about a decade older, both of which suited Jensen just fine. He was a good-looking guy, and totally rocking the salt and pepper look. 

His grip was firm, confident.

"That's me. And you must be Jensen," Jeff said, with a broad smile that soothed Jensen's nerves even more. It was an attractive look, and comforting in its warmth. "Good to meet you."

"Likewise," Jensen said, and it was almost true. He offered a flirty smile in return. "Even if I can't decide if I think you're daring or crazy for answering my flyer."

Jeff arched an eyebrow. "I'm pretty sure a similar thing could be said of you for putting it up in the first place."

"Oh, definitely," Jensen agreed. "But I already knew that. You're the unknown quantity here."

That earned him a chuckle. "I think there might be a hole in that logic somewhere. But it's a fair question."

"Does it have an answer?" Jensen asked, with passable nonchalance. 

"Your flyer was… memorable. And, with all due respect, have you seen yourself?" Jeff's gaze was openly appreciative as he looked Jensen up and down. "Like any red-blooded man would pass up that chance."

Well. At least he was honest.

"Now," Jeff said, while Jensen was still figuring out how he ought to respond to that. "If you're suitably reassured that I'm probably not an axe murderer, would you like to grab a coffee?"

What the hell. It was what he'd come for, after all. "Yes, I think I would."

They went through the rigmarole of ordering their drinks, then found themselves a quiet table.

And thus began Jensen's least favourite part of every first date.

"So," he said into the awkward silence. "Tell me something about yourself."

"Besides the fact that I'm questionably sane for answering wanted ads? I work in publishing." Jeff's grin flashed. "Boring, I know."

Jensen offered him a self-deprecating smile that he knew looked damn good on him. "Hey, no judging here. I'm an accountant. I know from boring."

Jeff smirked. "So you spice up your life by finding avant-garde ways to date?"

"Something like that," Jensen said, because he didn't feel like getting into the whole bullied into it thing. "How about you? What do you do when you're not publishing?"

The conversation flowed smoothly enough from there, with a few expected stumbles as they worked through the awkwardness of getting to know each other. Jeff was an easy person to talk to and, from what Jensen could tell in an hour-long date, seemed to fit the criteria that Danneel had set for his perfect man.

They parted ways only after they'd made plans for a second date, and Jensen left feeling cautiously optimistic about his future for the first time since he'd kicked James out on his ass.

Not that he was going to tell Danneel that, of course.

His other first dates didn't go anywhere, but the second date with Jeff was good enough to start them moving beyond awkwardness into something that could have been the start of a real relationship. In a rare moment of optimism, Jensen even cancelled plans with Chris and Steve on Sunday to fit in that watershed third date.

"I hope getting laid was worth ditching our gig," Chris said the next day at work, his tone somewhere between goading and put out. Because he was secretly five years old. 

"It was, actually," Jensen answered breezily. "Maybe you should try it."

"Son, the day I need dating advice from you is the day I shave my head and become a monk." Chris cocked his head, his eyes intent on Jensen's. "So you like this guy?"

Jensen made a face at him. "Oh god, I don't need you asking me about my love life. What the hell's wrong with you?"

Casually, Chris clipped him upside the head, ignoring Jensen's cry of protest. "Don't even start. I've had to do nothing but hear about your fucking love life for weeks. I just wanna know if I'm gonna have to deal with you crying into your beer again if things go sour with this Jeff guy."

"Funnily enough," Jensen said, rubbing at his sore head. "I'm not really feeling the love here."

"Don't make me hit you again. You know I'll enjoy it."

"Sadist. He's fine, I guess," Jensen said, with a sigh. "I hardly know him, really. We've only been out a couple of times."

"Hmm." Chris eyed him narrowly for a long moment before sitting abruptly back in his chair. "Fair enough. Just warn me in advance if you want me to kick his ass for you. Or if I have to stock up on tissues."

"Jackass," Jensen told him, because it was a million times better than admitting that it was nice to know that Chris cared. "Things are fine for now. If I have a sudden need for Häagen-Dazs and tissues, I'll let you know."

"Like fuck you will. That's Danni's job."

In the end, Jensen's cautious optimism about Jeff lasted all of two and a half weeks.

It was hard to say what went wrong, honestly. They went out a handful of times, and Jensen liked him well enough, but...

"Maybe I'm broken," Jensen said to himself, which was yet more proof that he ought to get a dog, if only so he'd have something to talk to other than the walls in his apartment. "He's hot and smart and everything I'm supposed to be looking for. And here I am figuring out how to break up with him."

He'd originally been intending to bring Jeff down to meet the gang tonight. It was Chad's birthday and, while Chad was someone that Jensen would only admit to considering a friend under _extreme_ duress, birthdays were pretty much the only time their entire chaotic, vaguely incestuous friends group managed to get together, so it was a good opportunity to get the entire 'meeting the friends' thing done in one fell swoop.

But the idea of introducing Jeff to his friends had been sitting uneasily under his skin all week, and Jensen had more than enough failed relationships behind him to know better than to ignore that feeling. There was nothing _wrong_ with Jeff. Quite the opposite, in fact. And the sex was pretty darn fantastic.

But that didn't mean that continuing to go out with Jeff was the _right_ choice, either. Dammit.

He headed over to Jeff's with a heavy heart, because breaking up with someone was never a fun thing to do. Jensen could tell that at least some of what he was feeling must have been showing on his face, because Jeff took one look at him and opened the door wider. "Come in."

Jensen did so. "Er, hi," he said awkwardly. 

"Hi," Jeff said, not moving to let Jensen further into the house. 

Apparently they were doing this in the hallway. Okay.

"Look, uh," Jensen scrubbed a hand through his hair. "I don't really know how to... it's not... I don't mean to-" Taking a firm hold on his courage, Jensen blurted out, "This really isn't working for me."

"Yeah," Jeff said unexpectedly. Jensen looked up to find him wearing a strange look of wistful resignation. "I kind of figured that might be the case."

Jensen blinked. "Uh... not really the reaction I was expecting."

That earned him a shrug and a self-deprecating sort of smile. "I mean, I definitely wish we were having a different conversation, but I get it. We never quite had that spark, did we?"

Personally, Jensen didn't think he'd had something that he'd define as a 'spark' in his entire goddamn dating career, but he supposed the point stood. "Guess boyfriend ads aren't that reliable then."

"Maybe not," Jeff said. "But it was still worth the try."

Jensen left Jeff's feeling at once relieved and melancholy, which was a seriously fucked up kind of mood that he was very much looking forward to drinking away. Of course, thanks to the delay, he was the last one to arrive at South 16, and so he was entirely unsurprised to find that Chad's party had taken over a good third of the bar and that most of his friends were already half in the bag. Par for the course at Chad parties, really.

"Casanova!" Chris hollered, as soon as Jensen walked in. "The fuck are you doing here?"

"I was invited, asshole!" Jensen shouted back, weaving his way through the crowded room until he fetched up at Chris' side. "So you can just fuck right off." 

"Thought you'd be too busy with the future Mr. Ackles to spend time with us!"

Jensen rolled his eyes. "Since when do I c-?"

"Jensen's getting married?" a too-loud voice asked. 

"Holy fuck, Jensen's getting married?"

"Congrats, Ackles!"

"That’s not what he meant!" Jensen tried, but it was too late. Truth was meaningless in the face of two dozen drunk-ass idiots who'd already heard everything they needed to.

Voices exploded around the table.

"I can't believe you didn't tell us!"

"Who did the proposing? Wait, who the hell are you even dating?"

"You're not back together with James, are you?"

Chris, the bastard, burst out laughing.

Jensen glared at him. "Couldn't at least have waited until I was drunk before getting into this shit?" he demanded over the noise.

"Nope!" Chris said gleefully. "Serves you right!"

Jensen would have asked him what he'd done to deserve this, but he was distracted by a hand on his arm. 

"Jensen!" It was Genevieve's friend, Jared, blinking at him with owlish, drunken eyes. "Jensen, are you really getting married?"

"No!" Jensen said, fighting the urge to roll his eyes.

"Oh," Jared said. There was a beat, and then he said, "Then what's Chris talking about?"

Jensen tried to shrug it off. "He thinks he's funny, is all."

Unfortunately, Chris was a jackass. "This loser thinks he's going to find love with a want ad!"

"Hey!" Danneel protested, appearing from out of the ether to drop down in the chair on Jensen's left. She was bright-eyed and flushed with alcohol. "It's a fucking great idea!"

Chris snorted. "Great, my ass. Look at this," he said, shoving his phone nearly up Jared's nose in his enthusiasm. "These two stuck this poster up all over the goddamn city in the hopes of getting Jensen married off."

"What?" Jensen protested. "No, we didn't!"

"We kind of did, actually," Danneel said, ignoring Jensen's strangled groan of outrage. 

"Huh," Jared said, squinting at the photo. His eyes flicked over to Jensen. "Is it working?"

Jensen sighed. "Not really."

"What?" Danneel straightened. "But that Jeff guy! You said he was great in the sack!"

And this was why Jensen hated drunk people when he wasn't one of them. "I did and he was," he gritted out from between clenched teeth. "But that doesn’t mean I want to marry the guy."

"So you _are_ trying to get married off," Jared concluded. His expression was almost verging on a pout, which looked ridiculous on a man Jared's size.

"I'm _not_ getting married," Jensen said, as firmly and as loudly as possible. 

"But…" Danneel was looking tragically betrayed. "What went wrong?"

Jensen shrugged awkwardly. "It wasn't really working out. No biggie."

"Typical," Chris sighed. "If you end up alone forever, it's cause you're too god damn picky. I hope you know that."

Danneel seized Jensen's hands in hers. "Please don't give up!"

"Who said I was giving up?" Jensen demanded. 

Danneel appeared not to hear. "It's just a small setback. You'll find someone," she said, with teary-voiced gravity. "I promise."

Jensen threw a desperate look Jared's way, hoping to derail this disaster before it got any worse, but Jared seemed to have lost interest in the conversation, if the way he was staring morosely into his beer was any indication.

Just then, Chad barreled into the conversation, both literally and figuratively.

"What's up, fuckers!" he demanded, throwing himself at Jared.

"Ack!" Jared cried, flailing as Chad landed half in his lap and half on the table.

"Jensen's moping about his love life," Chris said, so Jensen hit him.

"No, I'm not!"

"Jesus Christ," Chad said. "Can you fuckers talk about something else? My balls are trying to retract into my fucking anus thanks to all this girly shit. Time for birthday shots!"

The whole table cheered, and Jensen privately resolved never to talk about his personal life in public again. His friends were going to be the death of him.

And so, back to the dating drawing board Jensen went.

He'd kept getting hits from the posters while he'd been seeing if things with Jeff went anywhere, and it was less daunting this time around to commit to actually showing up for the dates he scheduled. Jeff had been a good guy, even if he hadn't been the right guy; surely Jensen would find someone else who _was_ the right guy. 

So he went out with Sterling. 

And Rob. 

And Mark. 

And Matt. 

And. And. And.

It got to be a pattern: go through his messages to find someone who sounded okay, set up a date, go on said date, fail utterly at feeling any mystical spark with the guy, go home dejected and generally regretting his entire existence.

Sometimes, Jensen felt like his life was actually the plot of a shitty Lifetime Movie. He just hoped that it meant he'd get the happy ending if he kept trying long enough.

His friends were supportive, in their own way.

"No soulmate yet?" Steve asked him, between holes on the golf course.

"Not yet," Jensen agreed. "Not ever, with the way things are going right now."

"Sorry to hear that. You getting laid at least?"

Jensen had to laugh. "Not as much as you'd think."

Steve shook his head. "Fucking criminal."

"Amen to that."

The dating continued. Jensen continued to have no fucking luck whatsoever.

Adopting a puppy was looking like a better and better option.

This. This was the moment when Jensen was 100% convinced that the universe was fucking with him.

For the first time since this whole ridiculous debacle had begun, Jensen felt a genuine connection with his date. Tahmoh was hot and smart and had a sense of humour that matched Jensen's. Their conversation had flown easily all evening, and Jensen had discovered that they had a lot of things in common. Tahmoh liked dogs, football and volunteered at the local recreation centre in his spare time. He was, Jensen had to admit, pretty much exactly the kind of guy he'd been hoping to meet. 

There was just one problem.

"So these guys are standing there being all smug," Tahmoh was saying, eyes alight with fondness at the memory. "And Stephen gives them this eat-your-face kind of grin and tells them - in fucking French - that shit talking people in foreign languages only works when they're not bilingual. You should have seen their faces!"

Tahmoh looked at him expectantly. Jensen considered and discarded several responses.

"Stephen sounds like a real character," he settled on. "Uh, how long were you guys together?"

"Two years," Tahmoh said, with a shrug that was meant to make it seem like it wasn't a big deal. Jensen wasn't buying it. "Fuck him, right?"

"Uh," Jensen said. "You do realize that every single story you've told tonight has been about him, right?"

It was Tahmoh's turn to scrabble for words. "Shit, really?"

"'Fraid so."

There was a pause.

"Shit," Tahmoh said, half-laughing. "I'm so sorry. This is a hell of a date; all I can do is talk about my ex."

"Seems to me like you're not really over him," Jensen said carefully. "Can I ask what happened?"

Which earned him a whole flood of information about Tahmoh's ex-boyfriend. Jensen offered some reciprocal sharing of some of his own relationship disasters to balance them out, and somehow, they managed to spend three hours talking about how bullshit dating was, long and short of which was that Tahmoh made the decision to reconnect with Stephen so he could get some real closure. Or get his boyfriend back. Whichever one worked out better.

So, not really a successful date, but a strangely enjoyable night out nonetheless.

"You should put up more posters," was Danneel's advice when she heard of his resounding lack of success.

Jensen groaned. "How is that going to help?"

Danneel sniffed. "Oh, ye of little faith. It's been nearly a month; you need fresh exposure."

"This isn't an ad campaign."

"Of course it is." She reached for her bag. "I made some new designs for you to choose from. Do you think we should put them up further afield this time? You might have exhausted the gay community around here."

"For the love of God, please stop!"

Jensen ended putting up more posters. Fucking Danneel.

Jensen was getting to be an expert at first dates.

"This has been great, but I've got to get back to the office. Call me," Tom said, with an admittedly gorgeous smile.

Jensen managed a non-committal nod in response. They both knew he wasn't going to.

Tom left, weaving through the scatter of tables on the patio and looking very attractive while doing so. Sadly, the view did absolutely nothing for Jensen.

With no pressing hurry to get back to his own job - he'd taken a half day - Jensen sighed and slumped back in his chair. "Another day another failure," he sighed to himself.

"Jensen?"

Craning his head, Jensen was greeted with the sight of Jared standing on the sidewalk just beyond the patio, a politely curious expression on his face. He was dressed in a pair of green scrubs and a light jacket in deference to the hint of fall in the air. 

"I didn't know you worked at a hospital," was what Jensen said instead of a proper greeting, because he was kind of a failure.

Instead of taking offense at Jensen's inability to act like a normal human being, Jared grinned. "That's probably because I'm a vet. I work at the clinic just off Main."

"Ah," Jensen said intelligently. "Sorry."

"Not to worry." Jared's head cocked. "Is everything okay? You look kind of… defeated."

Jensen huffed out a humorless laugh. "That's a good way to put it, yeah." He waved a hand at Tom's recently abandoned chair. "You want to sit? I can't say I'm exactly good company right now, but it's better than talking across the fence. Unless you have somewhere to be."

"I've got a little time before my lunch break's over," Jared said, coming over. His shoes nudged against Jensen's as he sat down, long legs sprawling to fill most of the space beneath the table. "So, you didn't answer my question."

"What question?"

"Is everything okay?"

"Oh," Jensen said. "Yeah, I guess."

The look that Jared gave him was unexpectedly penetrating. "Bullshit. No one sits around looking like their dog just died when everything's okay."

Jensen sighed. "It's nothing serious," he amended. "Just another failed date."

The worry on Jared's face shifted into something lighter. "That sucks," he said, blunt but honest. "Ever wish you could just skip the dating and move straight on to the good stuff?"

"God yes," Jensen said, feelingly. "I've gone on more first dates in the last month than I think I have in the past three years put together. It's exhausting."

"So that ad of yours is working then?" Jared asked, with an idleness that wasn't quite casual. Jensen wondered if he was thinking of trying it himself. Or, no, Jared had a boyfriend right now, didn't he? 

Jensen stifled a wholly childish surge of jealousy at the thought. Why did everyone have things figured out except for him?

Jared was still looking at him expectantly, so Jensen dredged up a wry smile. "Depends on your definition of 'working'. Cause it's been great for getting me dates, but not so great at starting something permanent."

"My mama always says you have to kiss a lot of frogs before you find a prince charming," Jared offered. 

"At this point, I'd even accept a prince not-so-bad-when-you-get-to-know-him." Jensen sighed. "It's either that or start resigning myself to a future of lonely isolation."

"Aw, don't say that."

Jensen snorted. "Because I'll find the right guy if I keep looking? I'm starting to doubt that particular gem of wisdom."

Jared grinned. "Actually, I was going to say that the rest of us haven't got a prayer if a guy who looks like you can't win at dating, but hey," a Gallic shrug. "Yours is good too." 

Jensen surprised himself by chuckling. "Is it terribly egoistic to admit that I kind of agree with you?"

"Sort of," Jared agreed. "But I promise I won't tell anyone. Hey, maybe you should audition for one of those reality-TV dating shows. They like pretty people, and it sounds like you can't fall much lower than you already have. I mean really, want ads?" 

"You're too kind," Jensen deadpanned. "As soon as they create that long-awaited fusion of _The Bachelor_ and _Queer Eye for the Straight Guy_ , I'll get right on that." 

Jared's laugh was bright. "Surprising that someone hasn't cashed in on that target audience yet."

"Shocking," Jensen agreed, somewhat surprised to find himself grinning as well.

They sat there smiling at each for a moment, and it was a comfortable kind of silence, the sort that had been in short supply in Jensen's life since he'd started dating complete strangers on a regular basis.

Jared licked his lips. "Hey, Jensen," he started, only to be cut off by his phone beeping out a cheery tone. He shut it off with a hurried jab of his thumb. "Shit, that's my alarm, sorry. Time to get back to work."

"You time your lunch break?" Jensen asked. "That seems awfully anal."

Jared's answering grin was ruefully amused. "If you worked with Addi, you would too. She's not the kind of person you keep waiting."

"I have no idea who Addi is, but I'll take your word for it." Jensen raised his coffee cup in a toast. "Nice to see you, Jared. Thanks for the company."

"Likewise," Jared said, rising to his feet and fairly towering over Jensen in the process. "Good luck with the search for true love."

"Oh, get the hell out of here," Jensen ordered, feeling considerably more cheerful now than he had before Jared had come by. It was a shame they'd never been closer friends; Jared was good company.

And he supposed that it was good that _someone_ was amused by his situation, at least.

Jensen opened the door. "Hey, Chr-"

Chris held up a warning hand. "I swear to God, if you say one word about your dating problems tonight, I will punch you in the face. In the _face_. You got that?"

"I got that," Jensen said, deciding to be amused instead of indignant. He offered Chris an innocent smile. "I thought you were here to watch some football, anyway."

"Damn straight," Chris agreed, and stomped past him towards the den. "You ordered the food yet?"

Jensen rolled his eyes. "Yes, your majesty," he deadpanned, closing the door.

They talked about nothing of consequence as they got themselves settled, and then quieted down to watch as the game started. 

"But seriously," Chris said, four minutes into the first. His eyes didn't leave the TV. "You having any luck at all?"

Jensen shrugged, not looking over. "Few second dates. One or two thirds. Nothing Earth shaking."

"Huh. Sucks to you," Chris said.

"Pretty much," Jensen agreed, and nothing more was said about it for the remainder of the night.

Sometimes, he found himself feeling somewhat absurdly grateful for his friends.

And then there were some people whose encouragement he could have lived without.

"Yo, Ackles!" Chad yelled, because he apparently believed that inside voices were for pussies. "I haven't got a wedding invite yet!"

Jensen rolled his eyes. "That's because I'm not getting married."

Chad squinted at him. "You sure about that? Way I hear it, you're dating half the queers in town."

"And not marrying any of them." Jensen sighed. "Why do you even care?"

"Don't want to miss out on the open bar," Chad answered blithely.

Jensen snorted. "Like hell I'd be stupid enough to have an open bar at a wedding with you at it." 

Chad shrugged. "Who says I'm gonna need you to invite me?"

"You crash my hypothetical wedding and I'm throwing your ass out."

"Promises, promises." Chad squinted at him. "You really still single?"

Why was Jensen even having this conversation? "Not that it's any of your damn business, but yes."

"Hmm. Guess you better get a move on, Ackles. You're not gonna be pretty forever." 

"Thanks for that, I guess. Can we talk about something else now?"

"Fucking A. This romance shit gives me hives."

"You're the one who started this conversation!"

"Tomato, tomahto."

Exactly seven weeks and four days after the posters went up, Jensen officially gave up. Again.

"I give up," he said, dropping heavily into the chair across from Danneel. "Game over. Do not pass Go, do not collect $200."

"What happened?" Danneel asked because, for some unknown reason, she was actually a supportive friend who cared about his angst. 

"So, I went out with this guy, Misha," he explained, thumbing through the drinks menu and wondering if it was too early in the day to order something with rum in it. Probably. "Weird, but in a good kind of way. Hot. Crazy smart. Has, like, three dogs." He pulled out a phone to show Danneel the photo that Misha had sent him to set up their date. She leaned in to take a look.

"He's cute," she approved. "And he sounds like your type. What went wrong?"

Jensen dropped his phone on the table with a huff. "We had a difference of opinion about what this date was going to lead to."

Danneel winced sympathetically. "He was just looking for a booty call?"

"A third, actually."

"A… third?" 

"Apparently, his wife literally wrote the book on threesomes," Jensen offered.

There was a pause. "Ah," Danneel said delicately.

Jensen snorted. "Exactly." He buried his head in his hands. "Why is this so impossible?" 

"You've got to give it time," Danneel tried, but Jensen was tired of it.

"I _have_ given it time! Fucking hell, Danni, I've been out on at least three dates a week for almost two months. I could probably fill a phone book with the numbers that are still waiting on my answering machine. I don't even know how there are still single gay guys left in the cit-"

Jensen's phone chose that moment to vibrate into life, interrupting him mid-word.

He dropped his head to the table. "Noooo," he moaned.

He could _hear_ Danneel raising an elegant eyebrow at him. "Not going to answer that?"

"No way," Jensen mumbled into the table. "No more dates. I'm going to move to Canada and become one with the snow and ice. Fuck dating."

"Chris was right, you are a drama queen." Before Jensen could react, Danneel scooped his phone off the table and hit 'accept'. "Jensen Ackles' phone," she purred. "Can I help you schedule a date with him?"

"Danni!" Jensen hissed, but she just smirked and waved him back as the person on the other end said something Jensen couldn't make out.

Jensen hit his head against the table again.

"Oh!" she gasped suddenly, enough startled interest in her voice to draw Jensen's attention. 

Knowing Danneel, she was probably doing it on purpose for exactly that reason, but it didn't stop Jensen from wondering what could have surprised her that much about some random stranger answering Jensen's stupid ad.

Unfortunately, nothing on Danneel's end of the conversation was any help in figuring it out. "Not at all! Nothing ventured, nothing gained, right?" A laugh. "Honey, I thought you'd never ask. How's Friday? Seven works. Where should he meet you?" Danneel pulled out her own phone, fingers flying as she nodded along with whatever the guy was saying. "Mmhmm, yeah, okay, got it. Bye!"

She hung up and looked over at Jensen, positively radiating smug self-satisfaction.

Jensen arched an eyebrow at her. "I thought we were having a _Game of Thrones_ marathon on Friday."

Danneel waved a hand. "Khal Drogo can wait one more day."

"Honestly, if you wanted to postpone it forever, I wouldn't complain. There's something deeply concerning about your obsession with Jason Mamoa."

"Brat." She swatted him on the shoulder. "Just for that, I'm not telling you anything about your date on Friday."

"You do realize that it's going to be hard to find him without a name," Jensen drawled.

A careless shrug answered him. "Yours is more than distinctive enough. He'll find you."

"Oh yes," Jensen said dryly. "Because putting all the power in someone else's hands right from the beginning is definitely going to make this better than all the other disaster dates I've had in the past two months."

"It's your own fault for threatening to become an Eskimo." Danneel pulled out the sincere eyes, lower lip trembling to devastating effect. "I just want you to be happy, Jensen."

"I'd be happier if you agreed to give up on this stupid idea already." Jensen bit his lip. "Maybe there's just no guy out there for me after all."

Danneel laid a gentle hand on his arm. "You'll never find out if you give up so soon. Please say you'll go?"

"Fine," Jensen surrendered ungraciously. "But I reserve the right to say I told you so when I'm still alone and depressed at 40."

"Honey, if you get that far, then the world is a seriously messed up place."

Jensen successfully put most of the worry out of his head and focused instead on all sorts of important things like video games and binge-watching Netflix.

So what if Danneel had progressed from poster printing to actively setting up his blind dates? It was no worse than what he'd already been doing to himself. Nothing to worry about. At worse case, he was in for yet another failed date. At best, he'd owe her a favour for setting it up instead of letting him ignore the phone call and start his grand new life as a Canadian hobo.

Honestly, he wasn't holding out much hope for the latter, but there were worse things than delaying his embargo on love for one week.

So he went about his business as usual, and tried to limit his worry about Danneel's scheming as much as possible.

Unfortunately, he did such a good job of putting it out of his head that it wasn't until he got to the restaurant that realized that Danneel never had told him what name the reservation would be under.

"I can take your name if you want to wait in the bar," the girl at the front desk offered. "Who are you waiting for?"

Well, this was embarrassing. "Your guess is as good as mine," Jensen admitted. "It's kind of like a mystery blind date, I guess. Uh, if you see any lost looking gay guys, send them my way?"

The girl's eyebrows had been climbing steadily higher the longer Jensen spoke, but then she smiled. "I can do that. Good luck!"

Jensen managed a wan smile and made his way over to the bar, ears burning with embarrassment. He ordered a gin and tonic and resisted the urge to down the whole thing by the slimmest of margins. He was never letting Danneel meddle in his love life ever again.

"She didn't tell you," a voice said behind him.

Jensen whirled. "Jared?" he demanded incredulously, because that was absolutely Jared behind him, looking unexpectedly gorgeous in a fitted sweater and dark washed jeans.

"Yeah," Jared said. He offered Jensen a sheepish smile. "Uh, hi."

"You..." Jensen's head whirled as he tried to figure out what's going on. "You're my date?!"

"I thought Danneel was going to tell you," Jared said, which wasn't an answer except for the fact that it totally was. "I'll understand if you don't want to."

"What? No, that's ... fine. And wow, I'm being totally rude," he realized, with a half laugh. "Let's go get a table."

The hostess gave Jensen a subtle thumbs-up behind Jared's back as she handed them off to their server. Jensen appreciated the solidarity, even if he still wasn't quite sure what was going on.

"Sorry," was the first thing Jared said, once the server had taken their orders. "I didn't mean to throw you off your game."

Jensen waved a hand. "It's a first date. It's _supposed_ to throw people off their game."

Jared offered him an unexpectedly shy grin. "Still. You seemed pretty surprised."

"Well, yeah. Don't you have a boyfriend?" Jensen had to ask. "I was sure that..."

"We broke up last summer," Jared said, with a calmness that was edged with a strange sort of anticipation. "Not that long before you and James split, actually."

"Oh," Jensen said awkwardly. "I didn't know."

Jared shrugged. "I didn't make a big deal of it. You know how our friends get."

"Don't remind me," Jensen groaned. "I've never met a group of people who were so determined to be supportive and yet so shit at it. Did you know that even Chad gave me advice? I mean, badly and it was mostly insults, but still. That's gotta be a sign of an impending apocalypse."

Jared laughed and, weirdly, looked a little guilty. "Ah, actually, that's probably my fault."

"You sicced Chad on me? Cause I think that's grounds for ending this date right now."

"I won't judge you for Chris if you don't judge me for Chad," Jared offered.

"Deal," Jensen said automatically. "But you still need to explain what you have to do with Chad telling me to get married before I lose my looks."

"He really said- what am I saying, of course he did." Jared sighed. "Chad knew that I like you. He's been trying to convince me to ask you out for years."

Wait, what?

" _Years_?" Jensen was astounded. "Are you serious?"

Jared scrubbed an awkward hand through his hair. "Yeah."

"But that's… how? Why didn't you ask me out?" Jared didn't strike him as the kind of guy who lacked confidence, and Jensen would be lying if he said that he hadn't had a fantasy or two about Jared in the past. Jensen would probably have said yes, if he'd asked.

"It was kind of a missed opportunity thing," Jared said, which didn't really clarify matters.

"What do you mean?"

Unexpectedly Jared smiled, a sweet, wistful sort of look. "Man, I was all set to ask you out the first time we met - at that ball game, remember? You had a wicked sunburn and spent most of the game ragging on Chris, and every time you laughed, I was just mesmerized. But then your boyfriend called you and I figured, well, you weren't free." His mouth twisted wryly. "And then I met Mark, and we were still going strong when you and Charles broke up. And then when Mark left, you were sleeping with that lawyer guy, and then you were seriously on the rebound and I wasn't looking for anything, and things pretty much continued in the same pattern."

"Huh," Jensen said, thinking back and acknowledging that yes, Jared was right. "Are you telling me that we've never managed to be single at the same time until now?" No wonder his brain was having trouble with the idea of Jared as prospective boyfriend. It seemed like such a startlingly obvious conclusion now that he was thinking about it.

"Yep. It's kind of impressive, actually."

"What about now, though?" Jensen asked. He leaned across the table, peering up into Jared's face. "You could've asked me out months ago."

"So could you," Jared shot back. "I've seen you ask guys out before."

"I guess I never really thought about dating you," Jensen had to admit, and he could read the unsurprised acceptance on Jared's face.

"I figured. And we've known each other so long that it seemed like it would be incredibly fucking awkward if I asked you out out of the blue."

Yeah, Jensen could see that. "So, what changed your mind?"

Jared chuckled. "Chris shoving a picture of your poster up my nose, actually. All I could think was, fuck, I fit all of these requirements. So, when I saw one of your posters hanging up at the gym, I grabbed a tab." Jared put a hand in his pocket and pulled out a tattered, soft-edged scrap of paper with Jensen's name and cell number on it. "I've been carrying it around for weeks, trying to get up the nerve."

"Well," Jensen said, after a moment. "I'm glad you finally did."

Jared's smile was like the sun coming out. "Yeah?" he asked.

Jensen smiled back. "Yeah."

They sat there grinning goofily at each other until the food arrived, and the conversation shifted into something less intense as they mixed years of familiarity with the business of getting to know each other in a way they never had before.

It was, Jensen had to admit, probably the best first date he'd ever had.

"So," Jared said, after their plates had been cleared. He offered Jensen a wicked grin that was giving him all sorts of ideas. "What do you think the odds are that Danneel's pasting a photo of me onto your poster as we speak so that she can shove it in your face tomorrow?"

"Oh my God, she is absolutely doing that," Jensen groaned. "I hadn't even thought of that. And then she's going to lord it over me forever that her ridiculous idea worked."

That earned him a smile. "It did, huh? You seem pretty confident about that considering we haven't even finished our first date yet."

God, was this what being shy felt like? How embarrassing. "Well," Jensen said, with his best attempt at a nonchalant shrug. "What can I say? I think we've got that spark."

"Yeah?" Jared's smile deepened. "Awesome. Does that mean it's not too creepy to ask Danneel for a copy of her cut and paste masterpiece to hang on my wall?"

"Tell you what," Jensen said. "You stick around long enough and _I'll_ make one for you."

"How long is long enough? Because I'm pretty good with long term goals. If I've got to stick around for years to earn a poster, it's probably best to start planning now."

Jensen couldn't have held back his smile if he'd tried. "Let's try for getting through dessert first, Romeo. I'll let you know from there."

"Deal." 

Maybe Jensen wasn't doomed to be alone forever, after all. He had a good feeling about this one.

~fin

[Art Post](https://dancing-adrift.dreamwidth.org/16726.html)

**Author's Note:**

> **Please do not post my works on goodreads or any other third party website.**


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